Homecoming: The Retriever Bar
It’s a common story on the Eastern Shore: child grows up in a small, rural community, escapes as soon as possible after high school graduation, and moves away to the opportunities and adventure of the big city. But sometimes, that story has a post-script—the Eastern Shore’s prodigal sons and daughters return to the place they call home, ready to establish roots and give back to the Chesapeake communities they have never really been able to leave behind.
Neyah White and Thomas Kaylor are two of Chestertown’s repatriated progeny—men who pursued careers of acclaim in the West Coast food and bar scene, only to return back to the brick sidewalks and familiar small-town pleasantries of High Street. Together, they are pouring their considerable talents into a new Chestertown venture—The Retriever, a bar tucked into a narrow storefront in the historic downtown. Here, with White as operator and head barman and Kaylor as chef, they are providing Chestertown with, as White puts it, “the kind of lusty technical food and good booze Chestertown deserves.” It’s an establishment that aspires to be more than just a watering hole. For White and Kaylor, cultivating a convivial “third space” in their hometown is the ultimate way to sustain the community they love.
Kaylor and White were not friends growing up, but their stories are remarkably similar—both grew up in Chestertown and started working in the food and service industry as their first ‘real’ jobs. But their ambition would only take them so far on the Eastern Shore, and in their 20’s, both struck out for the big cities and bright lights of the West Coast.
Listening to the two of them recount their work experience over the last 15-20 years is like watching a game of ping pong played with a golden ball. White, a self-proclaimed “cocktail nerd,” was in the first wave of the West Coast artisanal cocktail renaissance, and lists off stints at San Francisco’s Clift Hotel, Bacar, Mecca, Nopa, and finally, as a brand ambassador for Suntory and Pernod/Ricaud. Kaylor’s kitchen experience is equally impressive, with turns at Campanile in LA, under Gordon Ramsey for Kitchen Nightmares, at Thomas Keller’s bistro, Bouchon, and later at Keller’s New York restaurant, Per Se.
But for both men, the call of the Eastern Shore was strong. White dreamed of bringing his wife, Brandywine, home to Chestertown to start a family and maybe set up a bar of his own—a hope that intensified every time he visited during the town’s annual Tea Party Festival. Kaylor’s short trips back to Chestertown to visit his large family started to feel somehow anticipatory, like it was simply time to come home.
In 2017, White and his wife bought a technicolor Victorian house on Cannon Street and he began fulfilling his vision in earnest by launching a pop-up bar, LTO (for “Limited Time Offer”) in the space formerly occupied by Andy’s, a beloved local establishment. White soon opened a bottle shop, The Decoy Room, next door, and Kaylor wandered in, having finally decided to move home himself to take his chances in Chestertown. The two got to talking—the way you do in a small-town bar—and a shared vision for a renovated space with a lush whiskey list and elevated bistro fare began to take shape.
The Retriever quietly opened in the Fall of 2019 and the momentum has been building ever since. The space itself has been utterly transformed from its LTO days and looks like you’ve wandered into a stylish, upscale hotel bar in Paris. Behind a glossy bar is a library’s worth of incredible bottles of whiskey, rye, bourbon, and scotch, all backlit by a gilded wall like a Renaissance Madonna. From these makings, White and his team concoct adventurous cocktails for an appreciative Chestertown clientele (Toki highball, anyone?).
In the kitchen, Kaylor is in his element, turning out beautiful, inventive versions of bistro classics like the Croque Madame, topped with rich Mornay sauce and an exclamatory sunny-side-up egg, or his Smash burger, with its flawlessly crisp edges and juicy center that took 7.2 iterations to perfect (each version was updated and annotated on the menu as Kaylor tweaked the recipe). The Retriever also boasts one of the Eastern Shore’s only shucked-to-order raw bars, and hungry patrons can savor stylishly presented half-shell Beausoleils from Nova Scotia alongside oysters harvested from the Rappahannock and the Chester River itself.
It’s still early days, but White and Kaylor have big ambitions—both want to refine service, continue to develop a personal, playful menu, renovate other parts of the building, add a beer garden space to the back—but it’s clear that their new Chestertown digs suit them just fine.
“I’m really excited when I walk in every day,” White says. “I feel fortunate to be home, and do what I love to do here.” And judging from the packed bar and humming dining room, the locals agree. A clever sign out front reads, “The Retriever: Come. Sit. Stay,” and so, obediently, we do.
The Retriever Bar and The Decoy Bottle Shop
337 ½ High Street, Chestertown, MD
Instagram Facebook
